2-Butyl-5-methoxy-4-methyl-2-(3-oxopentyl)-1-indanone → butyl-4,8-dimethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7852

Reaction equation

C([C:5]1([CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[CH3:14])[C:6]1=O)CCC>C(O)(=O)C.Cl.CCOC(C)=O>[CH2:13]([CH:18]1[CH:5]2[C:6]([C:7]3[C:12]([CH2:13]2)=[C:11]([CH3:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=3)=[C:21]([CH3:22])[C:20](=[O:23])[CH2:19]1)[CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of the crude diketone from step 1 in acetic acid (1 mL) and 6N HCl (1 mL) was stirred and heated in an oil bath at 100° C. for 5 hours. After cooling, the reaction mixture was diluted with EtOAc (20 mL), washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered, and the solvent evaporated under vacuum. The residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, using 5% EtOAc in CH2Cl2 as developing solvent, to afford 9a butyl-4,8-dimethyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (84 mg) as a gum.

Workup

temperatureAfter cooling
washwashed with water (10 mL) and brine (10 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent evaporated under vacuum
customThe residue was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates

Sources & evidence

ORD record: ord-619e723c7b9e4e91bac3e3dc222ad9ee
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Linked notes

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